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Remote-first: is it right for your startup?
The four risks of remote-first teams. Choose wisely.
I recently declined an offer to co-found a startup, even though the solo CTO building it had obvious pre-product traction.
You probably think, "OMG! Why would you do such a thing?! (Can I get their email?)." Here's why: the CTO wanted to build a 100% in-person team. And me... I'm in the "I'll dial in from the Airbnb" camp 🏝️
I'm not here to explain why remote work is awesome, though. Instead, I want to help you figure out whether it's appropriate for your company to take the risks associated with building a 100% remote culture — or not.
At startups, every decision carries a downside risk. Especially in the early stages, a startup's success is defined by the founders' ability to recognize, manage, and mitigate different types of risk.
Unsurprisingly, the skills required to build a thriving remote culture differ from those needed to create an in-person culture. If a founder without the requisite expertise tries to build a remote culture, they layer on an additional level of risk which they can't see, let alone manage. This is a great way to dig your company into a deep grave.
So, what are those skills and risks? Let's dive in.
When you're building a distributed organization, you're inevitably hiring across cultures.
Quickly, you end up in a situation where talented people run into the pitfalls of cross-cultural conflicts. The most insidious side-effect of them is a loss of trust.
"You're not speaking up enough."
"She's always late!"
"He's not proactive and only does what he's told."
"She's not direct enough in her feedback, making collaboration impossible."
"He's too direct. This is so rude, and I dread working with him."
Those are just some of the (quite real) phrases your future colleagues will use to describe their peers. In most cases, the root cause of each is a breakdown in cross-cultural communication across one of the 8 cultural dimensions identified by Eryn Meyer.
A founder skilled at building remote cultures will recognize this and help the team overcome the barriers. They could do that in one of three ways:
through cross-cultural coaching and conflict resolution
by hiring an external coach
by adjusting the hiring practices and screening for the candidate's ability to work cross-culturally.
Knowledge management and transfer
Every team has two types of knowledge: tacit and explicit. Tacit is the informal knowledge we pick up in water cooler conversations with colleagues, quick meetings, or workshops.
Tacit knowledge is implicit, and it's often not very well structured. But it's often exceptionally timely and, therefore, vital for the health and function of a company.
Explicit knowledge, on the other hand, is codified. It's your Notion space, your API manual, the explanations in your Git pull requests, and your Jira (or Coda) tickets.
Due to how easy it is to create and share tacit knowledge, many fast-moving in-person Seed and Series A startups have somewhat limited and outdated documentation. Truth be told, they probably don't need it.
In contrast, 100% remote startups — especially those with employees across time zones — can't rely on tacit knowledge. Gone are the unstructured encounters with peers and quick "let's grab a coffee and do a walking meeting" conversations. Nada.
Employees have to write things down. They must learn to tell stories, convince, and explain via clear, structured written language. That's hard even for native speakers of English, let alone folks for whom English is a second or third language.
This means that the founders who aspire to run a 100% remote team must think about
how to hire engineers for communication, not just their technical ability
how to help the team improve written communication skills
how to build a no-meetings culture of asynchronous communication (instead of requiring meeting notes after every call — what a waste of time)
Morale & Rapport
Few of us can instantly connect with another human via Zoom. Our noisy mics and grainy videos make it hard to build rapport and see our colleagues as living souls instead of task-completing machines.
It's not impossible, though. Building a team-level rapport in a fully remote, geographically dispersed organization with diverse cultures requires a deep understanding of how to work with humans, social finesse, and how humans work. (And no, not everything can be solved through Radical Candor because that book applies best to cultures of Anglo-Saxon origin. To others, not so much.)
Helping people improve is an arduous task in in-person cultures. It sometimes feels outright impossible in fully remote organizations.
Robust employee development programs rely on a strong rapport between employees and their managers and a deep understanding of individual motivations, goals, strengths, and weaknesses.
In other words, employee development is highly contextual. Building such a level of interpersonal and managerial context in remote-first organizations requires a systematic approach that leaders who are used to in-person cultures often don't have.
Hiring and bias
Hiring across cultures? Welcome to a whole new level of complexity in fairness and evaluation:
Does this candidate have poor communication skills? Or do they simply follow a principles-first pattern in structuring their answer?
Note: principles-first cultures practice deductive reasoning. One must develop the theory or complex concept before presenting facts or opinions. Begin all messages by building a theoretical argument before moving on to a conclusion. The conceptual principles underlying each situation are valued.
Is this candidate insincere and lying about their experience? Or do they come from a culture where good communication is sophisticated and layered, so you're expected to read between the lines?
Note: In high-context cultures, good communication is sophisticated, nuanced, and layered. Messages are both spoken and read between the lines. Ideas are often implied and not plainly explained.
None of this is easy. Remote-first cultures are not for everyone, and depending on your level of skill and comfort as a founder, your mileage may vary.
As long as you can manage the risks of remote-first work, you can reap the benefits of it, too.
Want to work with me?
If you’re a founder of a late-Seed or early Series A startup and need help with:
accelerating your product execution and the search for PMF
setting up product discovery
building a product team
Then let’s chat.
🚀 My calendar is open: https://calendly.com/evgeny-lazarenko/founder-product-coaching
Alternatively, you can hit me up on LinkedIn.